The present invention relates to substituted 2-benzoyl-cyclohexane-1,3-diones of the formula I 
where:
R1 and R2 are are each hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, xe2x80x94OR5, xe2x80x94OCOR6, xe2x80x94OSO2R6, xe2x80x94SH, xe2x80x94S(O)nR7, xe2x80x94SO2OR5, xe2x80x94SO2NR5R8, xe2x80x94NR8SO2R6 or xe2x80x94NR8COR6;
R3 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, xe2x80x94OR7, xe2x80x94SR7 or xe2x80x94NR7R10;
R4 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C4-C6-cycloalkenyl, C3-C6-alkynyl, xe2x80x94COR9, xe2x80x94CO2R9, xe2x80x94COSR9 or xe2x80x94CONR8R9, where the alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals mentioned and R9 of the radicals xe2x80x94COR9, xe2x80x94CO2R9, xe2x80x94COSR9 and xe2x80x94CONR8R9 may be partially or fully halogenated and/or carry one to three of the following groups:
hydroxyl, mercapto, amino, cyano, R10, xe2x80x94OR10, xe2x80x94SR10, xe2x80x94NR8R10, xe2x95x90NOR10, xe2x80x94OCOR10, xe2x80x94SCOR10, xe2x80x94NR8COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR8R10, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be substituted;
X is oxygen or NR8:
n is 0, 1 or 2;
R5 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R6 is C1-C6-alkyl or C1-C6-haloalkyl;
R7 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R8 is hydrogen or C1-C6-alkyl;
R9 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or benzyl;
R10 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl;
Q is a cyclohexane-1,3-dione ring attached in position 2 with or without substitution;
and agriculturally useful salts thereof.
The invention additionally relates to processes and intermediates for preparing compounds of the formula I, to compositions comprising them, and to the use of the compounds of the formula I or of compositions comprising them for controlling harmful plants.
2-Benzoylcyclohexane-1,3-diones are known from the literature, for example from EP-A 278 742, EP-A 298 680, EP-A 320 864 and WO 96/14285.
However, the herbicidal properties of these prior art compounds and their compatibility with crop plants are not entirely satisfactory.
It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.
We have found that this object is achieved by the 2-benzoyl-cyclohexane-1,3-diones of the formula I and their herbicidal action.
Furthermore, the invention provides herbicidal compositions comprising the compounds I and having a very good herbicidal activity. Additionally, the invention provides processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
The present invention also provides stereoisomers of the compounds of the formula I. Pure stereoisomers and also mixtures thereof are included.
The compounds of the formula I contain a carbon-nitrogen double bond and are therefore present as E isomers or Z isomers or as E/Z isomer mixtures. Furthermore, the compounds of the formula I may contain further carbon-carbon or carbon-nitrogen double bonds. The invention provides the pure geometric isomers and also mixtures thereof.
Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers and, if this is the case, are present as mixtures of enantiomers or diastereomers. The invention provides the pure enantiomers or diastereomers and also mixtures thereof.
The compounds of the formula I may also be present in the form of their agriculturally useful salts, the kind of salt generally not being important. The salts of those cations or the acid additon salts of those acids whose cations or anions, respectively, do not adversely affect the herbicidal activity of the compounds I are generally suitable.
Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where, if desired, one to four hydrogen atoms may be replaced by C1-C4-alkyl or hydroxyl-C1-C4-alkyl and/or one phenyl or benzyl, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
Anions of usable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Emphasis is given to compounds of the formula I according to the invention where the variable Q is a cyclohexane-1,3-dione ring of the formula II linked in position 2 
where II also represents the tautomeric formulae IIxe2x80x2 and IIxe2x80x3, 
where
R11, R12, R14 and R16 are each hydrogen or C1-C4-alkyl;
R13 is hydrogen, C1-C4-alkyl or C3-C4-cycloalkyl, where the last two groups may carry one to three of the following substituents: halogen, C1-C4-alkylthio or C1-C4-alkoxy; or
is tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl; 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the last 6 radicals mentioned may be substituted by one to three C1-C4-alkyl radicals;
R15 is hydrogen, C1-C4-alkyl or C1-C6-alkoxycarbonyl; or
R13 and R16 together form a xcfx80-bond or a three- to six-membered carbocylic ring; or
the CR13R14 unit is replaced by Cxe2x95x90O.
Emphasis is also given to compounds of the formula I according to the invention where
R4 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C4-C6-cycloalkenyl, C3-C6-alkynyl, xe2x80x94COR9, xe2x80x94CO2R9, xe2x80x94COSR9 or xe2x80x94CONR8R9 where the alkyl, cycloalkyl, alkenyl-, cycloalkenyl and alkynyl radicals mentioned and R9 of the radicals xe2x80x94COR9, xe2x80x94CO2R9, xe2x80x94COSR9 and xe2x80x94CONR8R9 may be partially or fully halogenated and/or carry one to three of the following groups:
hydroxyl, mercapto, amino, cyano, R10, xe2x80x94OR10, xe2x80x94SR10, xe2x80x94NR8R10, xe2x95x90NOR10, xe2x80x94OCOR10, xe2x80x94SCOR10, xe2x80x94NR8COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR8R10, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be partially or fully halogenated and/or carry one to three radicals from the following group:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl.
The organic moieties mentioned for the substituents R1-R16 or as radicals on phenyl, hetaryl and heterocylyl rings represent collective terms for lists of the individual group members. All hydrocarbon chains, ie. all alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, alkyliminooxy, alkoxyamino, alkylthio, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, alkenyl, cycloalkenyl and alkynyl moieties, may be straight-chain or branched. Unless stated otherwise, preference is given to halogenated substituents carrying one to five identical or different halogens. Halogen is in each case fluorine, chlorine, bromine or iodine.
Furthermore, the following moities represent, for example:
C2-C4-alkyl: ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;
C1-C4-alkyl and the alkyl moieties of C1-C4-alkylcarbonyl: C2-C4-alkyl as mentioned above, and methyl;
C2-C6-alkyl, and the alkyl moieties of C1-C6-alkoxy-C2-C6-alkyl: C2-C4-alkyl as mentioned above, and pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;
C1-C6-alkyl and the alkyl moieties of C1-C6-alkoxy-C1-C6-alkyl: C2-C6-alkyl as mentioned above, and methyl;
C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, ie. for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;
C1-C6-haloalkyl: C1-C4-haloalkyl as mentioned above, and 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;
C1-C4-alkoxy and the alkoxy moieties of C1-C4-alkoxyamino, C1-C4-alkoxy-C2-C6-alkoxycarbonyl and C1-C4-alkoxycarbonyl: methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;
C1-C6-alkoxy and the alkoxy moieties of C1-C6-alkoxy-C1-C6-alkyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl and C1-C6-alkoxycarbonyl: C1-C4-alkoxy as mentioned above, and pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;
C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully subsstituted by fluorine, chlorine, bromine and/or iodine, ie. for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chlor-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;
C1-C4-alkylthio: methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;
C1-C4-alkylsulfonyl (C1-C4-alkyl-S(xe2x95x90O)2xe2x80x94): methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;
C1-C4-alkyliminooxy: methyliminooxy, ethyliminooxy, 1-propyliminooxy, 2-propyliminooxy, 1-butyliminooxy and 2-butyliminooxy;
C3-C6-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl;
C2-C6-alkenyl: C3-C6-alkenyl as mentioned above, and ethenyl;
C3-C6-alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn-1-yl, but-1-yn-3-yl, but-1-yn-4-yl but-2-yn-1-yl, pent-1-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-1-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl and 4-methylpent-2-yn-5-yl;
C2-C6-alkynyl: C3-C6-alkynyl as mentioned above, and ethynyl:
C3-C6-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
C4-C6-cycloalkenyl: cyclobuten-1-yl, cyclobuten-3-yl, cyclopenten-1-yl, cyclopenten-3-yl, cyclopenten-4-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl;
heterocyclyl and the heteroclyl [sic] radicals in heterocyclyloxy: three- to seven-membered saturated or partially unsaturated mono- or polycyclic heterocycles containing one to three hetero atoms selected from a group consisting of oxygen, nitrogen and sulfur, such as oxiranyl, oxetan-3-yl, thietan-3-yl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,3-dihydrofuran-4-yl, 2,3-dihydrofuran-5-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroxazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydropyrazol-3-yl, 2,5-dihydropyrazol-4-yl, 2,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dioxan-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 1,3-dioxolan-2-yl, 1,3-dithiolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2-yl,
hetaryl and the hetaryl radicals in hetaryloxy:
aromatic mono- or polycyclic radicals which, in addition to carbon ring members, may contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4,5-tetrazin-3-yl, and the corresponding benzo-fused derivatives.
All phenyl and hetaryl rings are preferably unsubstituted or carry one to three halogens and/or one or two radicals from the following group: nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy or methoxycarbonyl.
Preferred with a view to the use of the compounds of the formula I according to the invention as herbicides are those compounds where the variables have the following meanings, in each case either on their own or in combination:
R1 is nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, xe2x80x94OR5 or xe2x80x94S(O)nR7;
particularly preferably nitro, halogen such as, for example, fluorine, chlorine or bromine, C1-C6-haloalkyl, xe2x80x94OR5 or xe2x80x94SO2R7 such as, for example, methylsulfonyl, ethylsulfonyl or difluoromethylsulfonyl; especially preferably nitro, fluorine, chlorine, bromine, trifluoromethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonyl or difluoromethylsulfonyl;
R2 is hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, xe2x80x94OR5 or xe2x80x94S(O)nR7;
particularly preferably hydrogen, nitro, halogen such as, for example, fluorine, chlorine or bromine, C1-C6-alkyl such as, for example, methyl or ethyl, C1-C6-haloalkyl, xe2x80x94OR5 or xe2x80x94SO2R7 such as, for example, methylsulfonyl, ethylsulfonyl or difluoromethylsulfonyl;
especially preferably nitro, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonyl or difluoromethylsulfonyl;
R3 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl or xe2x80x94OR7;
R4 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl or C3-C6-alkynyl, where the last 4 substituents mentioned may be partially or fully halogenated and/or carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, xe2x80x94OR10, xe2x95x90NOR10, xe2x80x94OCOR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR8R10, C1-C4-alkyliminooxy, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy or hetaryloxy, where the last eight radicals mentioned may in turn be partially or fully halogenated and/or carry one to three radicals from the following group:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl;
particularly preferably C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl or C3-C6-alkynyl, where the last 4 substituents mentioned may be partially or fully halogenated and/or carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, xe2x80x94OR10, xe2x95x90NOR10, xe2x80x94OCOR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR8R10, C1-C4-alkyliminooxy, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy or hetaryloxy, where the last eight radicals mentioned may in turn be partially or fully halogenated and/or carry one to three radicals from the following group:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl;
X is oxygen or NH;
n is 0 or 2
R5 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, methoxyethyl, allyl or propargyl;
R7 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
particularly preferably methyl, ethyl, trifluoromethyl, difluoromethyl, methoxyethyl, allyl or propargyl;
R8 is hydrogen or C1-C6-alkyl;
R10 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R11, R12, R14 and R16 are each hydrogen or C1-C4-alkyl;
particularly preferably hydrogen, methyl or ethyl;
R13 is hydrogen, C1-C4-alkyl, C3-C4-cycloalkyl, where the last two groups may carry one to three of the following substituents: halogen, C1-C4-alkoxy or C1-C4-alkylthio; tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithian-2-yl or 1,3-dithiolan-2-yl, where the last six groups mentioned may in each case carry one to three C1-C4-alkyl radicals;
particularly preferably hydrogen, methyl, ethyl, cyclopropyl, di(methoxy)methyl, di(ethoxy)methyl, 2-ethylthiopropyl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 5,5-dimethyl-1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl, 5,5-dimethyl-1,3-dithian-2-yl or 1-methylthiocyclopropyl;
R15 is hydrogen, C1-C4-alkyl or C1-C4-alkoxycarbonyl;
particularly preferably hydrogen, methyl or methoxycarbonyl.
It may also be advantageous for R13 and R16 to form a xcfx80-bond, thus forming a double bond system.
The CR13R14 unit may also be advantageously replaced by Cxe2x95x90O.
Particular preference is given to compounds of the formula Ia ( I where R1 is attached in position 4 of the phenyl ring and R2 is attached in position 2 of the phenyl ring). 
Very particular preference is given to the compounds of the formula Ia in which R1 to R3, Q and X are as defined above and
R4 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl or C3-C6-alkynyl, where the last 4 substituents may be partially or fully halogenated and/or carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, xe2x80x94OR10, xe2x95x90NOR10, xe2x80x94OCOR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR8R10, C1-C4-alkyliminooxy, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy or hetaryloxy, where the last eight radicals mentioned may in turn be partially or fully halogenated and/or carry one to three radicals from the following group:
nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl.
Most particular preference is given to the compounds Ia1 ( I where R1=Cl, R11, R12, R13, R14, R15, R16=H, R1 being attached in position 4 of the phenyl ring and R2 being attached in position 2 of the phenyl ring), in particular the compounds of Table 1.
Furthermore, most particular preference is given to the following 2-benzoylcyclohexane-1,3-diones of the formula I:
the compounds Ia2, in particular the compounds Ia2.001-Ia2.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R13 is methyl: 
xe2x80x83the compounds Ia3, in particular the compounds Ia3.001-Ia3.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R13 and R14 are each methyl: 
xe2x80x83the compounds Ia4, in particular the compounds Ia4.001-Ia4.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R15 and R16 are each methyl: 
xe2x80x83the compounds Ia5, in particular the compounds Ia5.001-Ia5.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia6, in particular the compounds Ia6.001-Ia6.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R11, R15 and R16 are each methyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia7, in particular the compounds Ia7.001-Ia7.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R11, R12, R15 and R16 are each methyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia8, in particular the compounds Ia8.001-Ia8.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is nitro: 
xe2x80x83the compounds Ia9, in particular the compounds Ia9.001-Ia9.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is nitro and R13 is methyl: 
xe2x80x83the compounds Ia10, in particular the compounds Ia10.001-Ia10.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is nitro and R13 and R14 are each methyl: 
xe2x80x83the compounds Ia11, in particular the compounds Ia11.001-Ia11.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is nitro and R15 and R16 are each methyl: 
xe2x80x83the compounds Ia12, in particular the compounds Ia12.001-Ia12.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is nitro and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia13, in particular the compounds Ia13.001-Ia13.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is nitro, R11, R15 and R16 are each methyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia14, in particular the compounds Ia14.001-Ia14.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is nitro, R11, R12, R15 and R16 are each methyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia15, in particular the compounds Ia15.001-Ia15.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is methylsulfonyl: 
xe2x80x83the compounds Ia16, in particular the compounds Ia16.001-Ia16.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is methylsulfonyl and R13 is methyl: 
xe2x80x83the compounds Ia17, in particular the compounds Ia17.001-Ia17.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is methylsulfonyl and R13 and R14 are each methyl: 
xe2x80x83the compounds Ia18, in particular the compounds Ia18.001-Ia18.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is methylsulfonyl and R15 and R16 are each methyl: 
xe2x80x83the compounds Ia19, in particular the compounds Ia19.001-Ia19.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is methylsulfonyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia20, in particular the compounds Ia20.001-Ia20.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is methylsulfonyl, R11, R15 and R16 are each methyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia21, in particular the compounds Ia21.001-Ia21.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is methylsulfonyl, R11 R12 R15 and R16 are each methyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia22, in particular the compounds Ia22.001-Ia22.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is trifluoromethyl: 
xe2x80x83the compounds Ia23, in particular the compounds Ia23.001-Ia23.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is trifluoromethyl and R13 is methyl: 
xe2x80x83the compounds Ia24, in particular the compounds Ia24.001-Ia24.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is trifluoromethyl and R13 and R14 are each methyl: 
xe2x80x83the compounds Ia25, in particular the compounds Ia25.001-Ia25.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is trifluoromethyl and R15 and R16 are each methyl: 
xe2x80x83the compounds Ia26, in particular the compounds Ia26.001-Ia26.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is trifluoromethyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia27, in particular the compounds Ia27.001-Ia27.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is trifluoromethyl, R11, R15 and R16 are each methyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
xe2x80x83the compounds Ia28, in particular the compounds Ia28.001-Ia28.180, which differ from the corresponding compounds Ia1.001-Ia1.180 in that R1 is trifluoromethyl, R11, R12, R15 and R16 are each methyl and the CR13R14 unit is replaced by Cxe2x95x90O: 
Extraordinary preference is given to the compounds of the formula Iaxe2x80x2  I where R1 is attached in position 4 of the phenyl ring and R2 is attached in position 2 of the phenyl ring) 
where
R1 is halogen or C1-C4-alkylsulfonyl;
R2 is halogen or C1-C4-alkyl, in particular halogen;
R3 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy, in particular hydrogen or C1-C4-alkoxy;
R4 is C1-C6-alkyl, C3-C6-alkynyl, where these two substituents may be partially or fully halogenated and/or may carry one to three of the following groups: phenyl or hetaryl, where these groups may in turn be partially or fully halogenated;
X is oxygen;
R11, R121 R13, R14, R15, R16 are each hydrogen or C1-C4-alkyl.
The 2-benzoylcyclohexane-1,3-diones of the formula I can be obtained in a variety of ways, for example by the following process:
Reaction of cyclohexanediones of the formula II with an activated carboxylic acid IIIxcex1 or a carboxylic acid IIIxcex2 which is preferably activated in situ, to give the acylation product IV, and activated subsequent rearrangement. 
L is a nucleophilically replaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, etc.
The activated carboxylic acid can be employed directly, as in the case of the acyl halides, or be generated in situ, for example by using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic acid esters, 2 pyridine disulfite [sic]/triphenylphosphine, carbonyldiimidazole, etc.
If appropriate, it may be advantageous to carry out the acylation reaction in the presence of a base. The reactants and the auxiliary base are advantageously employed in equimolar amounts. A slight excess of the auxiliary base, for example 1.2 to 1.5 molar equivalents based on II, may be advantageous in certain instances.
Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide and dimethyl sulfoxide, or esters such as ethyl acetate, or mixtures of these.
If acyl halides are used as activated carboxylic acid component, it may be advantageous to cool the reaction mixture to 0-10xc2x0 C. when adding this reaction partner. Subsequently, the mixture is stirred at 20-100xc2x0 C., preferably at 25-50xc2x0 C., until the reaction has ended. Work-up is carried out in a conventional manner, for example by pouring the reaction mixture into water and extracting the product of value. Suitable solvents for this purpose are in particular methylene chloride, diethyl ether and ethyl acetate. After drying off the organic phase and removal of the solvent, crude enol ester of the formula IV is preferably purified by chromatography. However, it is also possible to use the crude enol ester of the formula IV without further purification for the rearrangement.
The rearrangement of the enol esters of the formula IV to the compounds of the formula I is advantageously carried out at temperatures from 20 to 40xc2x0 C. in a solvent and in the presence of an auxiliary base and, if appropriate, with the aid of a cyano compound as catalyst.
Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, ethyl acetate, toluene or mixtures of these. The preferred solvent is acetonitrile.
Suitable auxiliary bases are tertiary amines such as triethylamine or pyridine, or alkali metal carbonates, such as sodium carbonate and potassium carbonate, which are preferably employed in equimolar amounts or in up to four-fold excess, based on the enol ester. Preference is given to using triethylamine, preferably in twice the equimolar amount, based on the enol ester.
Suitable xe2x80x9crearrangement catalystsxe2x80x9d are inorganic cyanides, such as sodium cyanide and potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin and trimethylsilyl cyanide. They are conventionally used in an amount of from 1 to 50 mol percent, based on the enol ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of from 5 to 15, preferably 10, mol percent, based on the enol ester.
Workup can be carried out in a manner known per se. For example, the reaction mixture is acidified with dilute mineral acid, such as, for example 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract may be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the resulting precipitate is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.
(Examples of the preparation of enol esters from cyclohexane-1,3-diones and of the cyanide-catalyzed rearrangement of the enol esters are given, for example, in EP-A 186 118, U.S. Pat. No. 4,780,127).
The cyclohexane-1,3-diones of the formula II used as starting materials are known or can be prepared by known processes (for example EP-A 71 707, EP-A 142 741, EP-A 243 313, U.S. Pat. No. 4,249,937; WO 92/13821).
The benzoic acid derivatives of the formula III are novel, 
where:
R1, R2 are each hydrogen, nitro, halogen, cyano, thiocyanato, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, xe2x80x94OR5, xe2x80x94OCOR6, xe2x80x94OSO2R6, xe2x80x94SH, xe2x80x94S(O)nR7, xe2x80x94SO2OR5, xe2x80x94SO2NR5R8, xe2x80x94NR8SO2R6 or xe2x80x94NR8COR6;
R3 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, xe2x80x94OR7, xe2x80x94SR7 or xe2x80x94NR7R10;
R4 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C4-C6-cycloalkenyl, C3-C6-alkynyl, xe2x80x94COR9, xe2x80x94CO2R9, xe2x80x94COSR9 or xe2x80x94CONR8R9, where the alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals mentioned and R9 of the radicals xe2x80x94COR9, xe2x80x94CO2R9, xe2x80x94COSR9 and xe2x80x94CONR8R9 may be partially or fully halogenated and/or carry one to three of the following groups:
hydroxyl, mercapto, amino, cyano, R10, xe2x80x94OR10, xe2x80x94SR10, xe2x80x94NR8R10,xe2x95x90NOR10, xe2x80x94OCOR10, xe2x80x94SCOR10, xe2x80x94NR8COR10, xe2x80x94CO2R10, xe2x80x94COSR10, xe2x80x94CONR8R10, C1-C4-alkyliminooxy, C1-C4-alkoxyamino, C1-C4-alkylcarbonyl, C1-C4-alkoxy-C2-C6-alkoxycarbonyl, C1-C4-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the last eight radicals mentioned may in turn be substituted;
X is oxygen or NR8;
n is 0, 1 or 2;
R5 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R6 is C1-C6-alkyl or C1-C6-haloalkyl;
R7 is C1-C6-alkyl, C1-C6-haloalkyl, C4-C6-alkoxy-C2-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R8 is hydrogen or C1-C6-alkyl;
R9 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or benzyl;
R10 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R17 is hydroxyl or a radical that can be removed by hydrolysis.
Examples of radicals that can be removed by hydrolysis are alkoxy, phenoxy, alkylthio and phenylthio radicals with or without substitution, halides, hetaryl radicals which are attached via nitrogen, amino and imino radicals with or without substitution, etc.
Preference is given to benzoyl halides IIIxcex1, where L=halogen  III where R17=halogen), 
where the variables R1 to R4 and X are each as defined under formula III and
L is halogen, in particular chloride or bromide.
Preference is also given to the benzoic acids of the formula IIIxcex2  III where R17=hydroxyl), 
where the variables R1 to R4 and X are each as defined under formula III.
Preference is also given to the benzoic acid esters of the formula IIIxcex3 ( III where M=C1-C6-alkoxy) 
where the variables R1 to R4 and X are each as defined under formula III and
M is C1-C6-alkoxy.
With regard to the preferred compounds of the formula III, the remarks made under the compounds I apply to the radicals R1 to R4 and X.
The compounds of the formula IIIxcex1 (where L=halogen) can be prepared in a similar manner to literature methods (cf. L. G. Fieser, M. Fieser xe2x80x9cReagents for Organic Synthesisxe2x80x9d, Vol. I, p. 767-769 (1967)) by reacting benzoic acids of the formula IIIxcex2 with halogenating reagents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride or oxalyl bromide.
The benzoic acids of the formula IIIxcex2 can be obtained in a similar manner to literature methods, inter alia by hydrolysis of the benzoic acid esters of the formula IIIxcex3 (where M=C1-C6-alkoxy).
The benzoic acid esters of the formula IIIxcex3 are obtainable in a variety of ways, for example by the following processes: 
Isophthalic acid derivatives of the formula VI can be obtained by oxidation of aldehydes of the formula V in a manner known per se (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd Edition, p. 629 ff, Wiley-Interscience Publication, 1985).
In a similar manner to literature methods, the compounds of the formula VI can initially be converted into the corresponding activated carboxylic acids VII where L1 is a nucleophilically displaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoracetate etc., and then into the corresponding hydroxamic acid or carbohydrazide derivatives of the formula VIII (Australian J. Chem. 22, (1969), 1731-1735; ibid 22 (1969), 161-173; J. Org. Chem. 27 (1974), 1341-1349).
Alkylation of compounds of the formula VIII leads to compounds of the formula IIIxcex3 (where R3=OR7) in a manner known per se (EP-A 463 989; Synthesis (1983), 220-222; U.S. Pat. No. 4,931,088; J. Org. Chem. 31 (1971), 284-294; J. Chem. Soc. Perk. II (1977), 1080-1084). 
Compounds of the formula IIIxcex3 are obtained in a manner known per se by reacting aldehydes/ketones of the formula IX with xe2x80x9calkoxamines or alkylhydrazinesxe2x80x9d. In a similar manner to processes known from the literature, it is possible to react aldehydes/ketones of the formula IX with hydroxylamine or hydrazine and to alkylate them subsequently (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd Edition, p. 359, p. 805-806, Wiley-Interscience Publication, 1985). 
It is possible to convert nitriles of the formula X in a manner known per se by alcoholysis (R7OH) into imino esters which can be reacted in a further step with hydroxylamines or hydrazines to give compounds of the formula IIIxcex3 (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd Edition, p. 792-793, Wiley-Interscience Publication, 1985; U.S. Pat. No. 4,965,390).
In a similar manner to processes known from the literature, nitriles of the formula X can be prepared from the corresponding aldehydes V (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd Edition, p. 806-807, Wiley-Interscience Publication, 1985). It is also possible to obtain nitrites of the formula X from anilines of the formula XI by employing the Sandmeyer reaction or from aryl halides of the formula XII by the Rosemund/von Braun reaction using metal cyanides, in particular CuCN (J. March, xe2x80x9cAdvanced Organic Chemistryxe2x80x9d, 3rd Edition, p. 594, p. 648, Wiley-Interscience Publication, 1985). 
In a similar manner to processes known from the literature, the aldehydes of the formula V can be prepared from the corresponding toluenes of the formula XIII by conversion into the xcfx89-halotoluene XIV and subsequent oxidation (cf. Synth. Commun. 22 (1992) 1967-1971). 